JP2009078991A - Thiophenecarboxylic acid derivative, method for producing the same, and fungicide - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a thiophene carboxylic acid derivative that exhibits excellent plant disease-controlling actions, particularly excellent controlling effects on rice blast disease while causing no injury or very little injury to useful crops. <P>SOLUTION: The thiophene carboxylic acid derivative is represented by general formula (1) [wherein R<SP>1</SP>and R<SP>2</SP>are each a hydrogen atom, a 1-6C haloalkyl group or the like (provided that at least one of R<SP>1</SP>and R<SP>2</SP>is a 1-6C haloalkyl group); R<SP>3</SP>is a hydrogen atom or the like; A is OR<SP>4</SP>, SR<SP>5</SP>, NR<SP>6</SP>R<SP>7</SP>or NR<SP>8</SP>NR<SP>9</SP>R<SP>10</SP>; R<SP>4</SP>is an 8-12C alkyl group or the like; R<SP>5</SP>is a 1-12C alkyl group or the like; R<SP>6</SP>and R<SP>7</SP>are each a hydrogen atom, an 8-12C alkyl group or the like; and R<SP>8</SP>, R<SP>9</SP>and R<SP>10</SP>are each a hydrogen atom, a 1-12C alkyl group or the like]. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a thiophenecarboxylic acid derivative, a method for producing the same, and a fungicide containing the same as an active ingredient.

Pest control plays a major role in rice cultivation, and various fungicides have been developed and used as an important disease especially for rice blast. However, a new bactericidal agent that can control harmful bacteria at a safe and low concentration is required due to environmental problems.
For example, it is already known that a thiophenecarboxylic acid derivative having a certain haloalkyl group has bactericidal activity (see, for example, Patent Document 1). In addition, it is known that certain thiophene-5-carboxylic acid derivatives having a haloalkyl group at the 2-position have bactericidal activity (see, for example, Patent Document 2).
JP-T-2006-521316 JP-T-2001-504832

However, the compound described in Patent Document 1 is limited to derivatives such as a structure having a trifluoromethyl group at the 4-position of thiophene-5-carboxylic acid, and includes 2-haloalkyl-5-thiophenecarboxylic acid derivatives and 3-haloalkyls. There is no specific description about -5-thiophenecarboxylic acid derivatives.
In addition, the compound described in Patent Document 2 is limited to a derivative having a structure having a substituted benzene ring at the 3-position of thiophene-5-carboxylic acid, and has a bactericidal activity, particularly in rice blast and other useful crops. There is not enough.
Furthermore, there is no description regarding the bactericidal activity of 2-haloalkyl-5-thiophenecarboxylic acid and 3-haloalkyl-5-thiophenecarboxylic acid.
It is an object of the present invention to provide a thiophenecarboxylic acid derivative that exhibits an excellent plant disease control action, particularly an excellent control effect on rice blast, and has no harmful effect on useful crops or is extremely harmless. To do.

The present inventors have synthesized various novel thiophenecarboxylic acid derivatives in order to solve the above-described problems, and have studied variously about their bactericidal activity. As a result, the present inventors have found a compound that exhibits an excellent plant disease control action, particularly an excellent control effect against rice blast, and has no harmful effect on useful crops or is extremely harmless.
That is, the present invention is as follows.
<1> A thiophenecarboxylic acid derivative represented by the following general formula (1).

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms. R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group. A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ . R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms. R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms.

<2> The thiophenecarboxylic acid derivative according to <1>, wherein R ¹ is a haloalkyl group having 1 to 6 carbon atoms, and R ² and R ³ are hydrogen atoms.
<3> The thiophenecarboxylic acid derivative according to <2>, wherein R ¹ is a fluoroalkyl group having 1 to 6 carbon atoms.
<4> The thiophenecarboxylic acid derivative according to <3>, wherein A is NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ , and R ⁶ and R ⁸ are hydrogen atoms.

<5> The method for producing a thiophenecarboxylic acid derivative according to any one of <1> to <4>, wherein the compound represented by the following general formula (2) and the following general formula (3): A method for producing a thiophenecarboxylic acid derivative, comprising a step of reacting a compound represented by the formula:

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms. R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group. A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ . R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms. R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms.

<6> The method for producing a thiophenecarboxylic acid derivative according to any one of <1> to <4>, wherein the compound represented by the following general formula (4) and the following general formula (3): A method for producing a thiophenecarboxylic acid derivative, comprising a step of reacting a compound represented by the formula:

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms. R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group. A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ . R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented. R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms. R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms. Y represents a leaving group. ]

<7> A bactericidal agent containing at least one thiophenecarboxylic acid derivative represented by the following general formula (5) as an active ingredient.

[Wherein, R ⁵¹ and R ⁵² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ⁵¹ and R ⁵² represents a haloalkyl group having 1 to 6 carbon atoms. R ⁵³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group. A ⁵⁰ represents OR ⁵⁴ , SR ⁵⁵ , NR ⁵⁶ R ⁵⁷ or NR ⁵⁸ NR ⁵⁹ R ⁶⁰ , and R ⁵⁴ and R ⁵⁵ each independently represent an alkyl group having 1 to 12 carbon atoms or 3 to 6 carbon atoms A cycloalkyl group, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and an aryl group which may be substituted and having 1 to 6 carbon atoms It represents an alkyl group, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted heteroaryl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. R ⁵⁶ and R ⁵⁷ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with An alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms It is. Here, R ⁵⁶ and R ⁵⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms. R ⁵⁸ , R ⁵⁹ and R ⁶⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁵⁹ and R ⁶⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms.
<8> The fungicide according to <7>, which is used for agriculture and horticulture.

<9> A fungicide containing as an active ingredient at least one thiophenecarboxylic acid represented by the following general formula (2).

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms. R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group]
<10> The fungicide according to <9>, which is used for agriculture and horticulture.

  According to the present invention, there is provided a thiophenecarboxylic acid derivative that exhibits an excellent plant disease control action, particularly an excellent control effect on rice blast, and has no harmful effect on useful crops or is extremely harmless. Can do.

  The thiophenecarboxylic acid derivative of the present invention is represented by the following general formula (1). By having a specific structure represented by the following general formula (1), it exhibits an excellent plant disease control action, particularly an excellent control effect on rice blast, and has no harmful effect on useful crops, or Very harmless.

In General Formula (1), R ¹ and R ² are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a carbon number. 1-6 haloalkoxy groups, C1-C6 alkylthio groups, C1-C6 haloalkylthio groups, C1-C6 alkylsulfinyl groups, C1-C6 haloalkylsulfinyl groups, C1 Represents a -6 alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms.

R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or 1 to 1 carbon atoms. 6 haloalkylthio groups, C1-6 alkylsulfinyl groups, C1-6 haloalkylsulfinyl groups, C1-6 alkylsulfonyl groups, C1-6 haloalkylsulfonyl groups, halogen atoms, cyano Represents a group or a nitro group.

In the present invention, from the viewpoint of a plant disease control effect, R ¹ is preferably a haloalkyl group having 1 to 6 carbon atoms, R ² and R ³ are preferably hydrogen atoms, and R ¹ is ¹ to 6 carbon atoms. More preferably, R ² and R ³ are hydrogen atoms, R ¹ is a fluoroalkyl group having 1 to 3 carbon atoms, and R ² and R ³ are hydrogen atoms. Is more preferable.

A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ .
R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.

In the present invention, from the viewpoint of controlling plant diseases, R ¹ is a haloalkyl group having 1 to 6 carbon atoms, R ² and R ³ are hydrogen atoms, and R ⁴ is an alkyl having 8 to 12 carbon atoms. Group, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and an aryl group which may be substituted Alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted heteroaryl group, an optionally substituted aryl group or an optionally substituted heteroaryl R ¹ is a fluoroalkyl group having 1 to 6 carbon atoms, R ² and R ³ are hydrogen atoms, R ⁴ is a cycloalkyl group having 3 to 6 carbon atoms, 2-6 alkenyl , A C3-C6 cycloalkenyl group, a C2-C6 alkynyl group, a C1-C6 alkyl group substituted with an optionally substituted aryl group, a substituted heteroaryl group It is more preferably an alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group, or a heteroaryl group which may be substituted.

R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.

R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.

R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.

In the present invention, from the viewpoint of a plant disease control effect, R ¹ is preferably a haloalkyl group having 1 to 6 carbon atoms, R ² and R ³ are preferably hydrogen atoms, and R ¹ is ¹ to 6 carbon atoms. It is more preferable that R ² and R ³ are hydrogen atoms, R ¹ is a fluoroalkyl group having 1 to 6 carbon atoms, and R ² and R ³ are hydrogen atoms. , A is NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ , and R ⁶ and R ⁸ are particularly preferably a hydrogen atom.

In the present invention, from the viewpoint of plant disease control effect, as the alkyl group having 1 to 6 carbon atoms, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.,
As an alkyl group having 8 to 12 carbon atoms, an octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc.
As the alkyl group having 1 to 12 carbon atoms, in addition to the alkyl group having 1 to 6 carbon atoms, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc.

Moreover, as a C1-C6 haloalkyl group, a trifluoromethyl group, a difluoromethyl group, a monofluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a tribromomethyl group, a trifluoroethyl group, Pentafluoroethyl group, trichloroethyl group, tribromoethyl group, trifluoropropyl group, perfluoropropyl group, etc.
Examples of the fluoroalkyl group having 1 to 6 carbon atoms include a trifluoromethyl group, a difluoromethyl group, a monofluoromethyl group, a trifluoroethyl group, a pentafluoroethyl group, a trifluoropropyl group, and a perfluoropropyl group.
Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy group, ethoxy group, propoxy group, butoxy group,
Examples of the haloalkoxy group having 1 to 6 carbon atoms include a trifluoromethoxy group, a trifluoroethoxy group, a trichloroethoxy group, a pentafluoroethoxy group, and a perfluoropropyl group.
Examples of the alkylthio group having 1 to 6 carbon atoms include a methylthio group, an ethylthio group, a propylthio group, and a butylthio group.

Examples of the haloalkylthio group having 1 to 6 carbon atoms include a trifluoromethylthio group, a trifluoroethylthio group, and a trichloroethylthio group.
As the alkylsulfinyl group having 1 to 6 carbon atoms, a methanesulfinyl group, an ethanesulfinyl group, etc.,
Examples of the haloalkylsulfinyl group having 1 to 6 carbon atoms include a trifluoromethanesulfinyl group, a trifluoroethanesulfinyl group, and a trichloroethanesulfinyl group.
Examples of the alkylsulfonyl group having 1 to 6 carbon atoms include a methanesulfonyl group and an ethanesulfonyl group.
Examples of the haloalkylsulfonyl group having 1 to 6 carbon atoms include a trifluoromethanesulfonyl group, a trifluoroethanesulfonyl group, and a trichloroethanesulfonyl group.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom,
Examples of the cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group,
Examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, and a hexenyl group.
Examples of the C3-C6 cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and the like.
Examples of the alkynyl group having 2 to 6 carbon atoms include ethynyl group, propynyl group, butynyl group, pentynyl group, hexynyl group,

As the aryl group, a phenyl group, a naphthyl group, etc.
Heteroaryl groups include pyridyl, pyrimidyl, pyridazyl, pyrazinyl, thienyl, furanyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, indolyl, quinolyl, and isoquinolyl groups , Benzofuranyl group, benzothienyl group, benzoxazolyl group, benzisoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzoisothiazolyl group, etc.
Examples of the heterocyclic group having 2 to 5 carbon atoms include morpholinyl, thiomorpholinyl, aziridinyl, pyrrolidinyl, piperidinyl, pyrrolyl and the like.

  Examples of the substituent for the aryl group and heteroaryl group include alkyl groups such as methyl group, ethyl group, propyl group and butyl group, aryl groups such as phenyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. A cycloalkyl group, a trifluoromethyl group, a difluoromethyl group, a halogen-substituted alkyl group such as a bromodifluoromethyl group and a trifluoroethyl group, an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group and a butoxy group, and a trifluoromethoxy group Halogen substituted alkoxy groups such as difluoromethoxy group and trifluoroethoxy group, alkylthio groups such as methylthio group, ethylthio group, propylthio group and butylthio group, trifluoromethylthio group, difluoromethylthio group and tri Halogen-substituted alkylthio groups such as trifluoroethylthio group, alkylsulfinyl groups such as methanesulfinyl group, ethanesulfinyl group, propanesulfinyl group and butanesulfinyl group, halogen-substituted alkyl such as trifluoromethanesulfinyl group, difluoromethanesulfinyl group and trifluoroethanesulfinyl group Alkylsulfonyl groups such as sulfinyl group, methanesulfonyl group, ethanesulfonyl group, propanesulfonyl group and butanesulfonyl group, halogen-substituted alkylsulfonyl groups such as trifluoromethanesulfonyl group, difluoromethanesulfonyl group and trifluoroethanesulfonyl group, acetylamino group , Such as acylamino group such as benzoylamino group, sulfonamido group and butanesulfonamido group Halogen-substituted alkylsulfonamide groups such as rusulfonamide group, trifluoromethanesulfonamide group, difluoromethanesulfonamide group and trifluoroethanesulfonamide group, halogen atoms of fluorine atom, chlorine atom, bromine atom and iodine atom, cyano group, Acyl groups such as nitro group, acetyl group and benzoyl group can be exemplified.

As the acyl group, an alkylcarbonyl group such as an acetyl group, an arylcarbonyl group such as a benzoyl group or a heteroarylcarbonyl group such as an optionally substituted isoxazolecarbonyl group, etc.
As an alkoxycarbonyl group, a methoxycarbonyl group, a propoxycarbonyl group, etc.,
As the aryloxycarbonyl group, a phenoxycarbonyl group, etc.
As the alkylsulfonyl group, a methanesulfonyl group, a propanesulfonyl group, etc.
As the arylsulfonyl group, a benzenesulfonyl group or the like,
As the alkylaminocarbonyl group, a methylaminocarbonyl group, a propylaminocarbonyl group, etc.,
Examples of the arylaminocarbonyl group include a phenylaminocarbonyl group.

  The method for producing a thiophenecarboxylic acid derivative of the present invention includes a step of reacting a compound represented by the following general formula (2) with a compound represented by the following general formula (3). That is, the thiophenecarboxylic acid derivative of the present invention can be produced by a reaction represented by the following reaction formula (1).

In Scheme ^(1), R ^1, R 2, ^{R 3} and A are respectively the same meanings as ^{R 1,} R 2, ^{R 3} and A in the general formula (1).
In the reaction formula (1), the thiophenecarboxylic acid represented by the general formula (2) and the compound represented by the general formula (3) are subjected to a condensation reaction in the absence of a solvent or in a solvent to obtain a general formula ( The thiophenecarboxylic acid derivative represented by 1) can be produced.

The thiophenecarboxylic acid represented by the general formula (2) can be produced, for example, by the method described in Journal of Fluorine Chemistry (1990), 46 (3), 445-449, etc.
In addition, when A in the general formula (3) is —NR ⁶ R ⁷ or —NR ⁸ NR ⁹ R ¹⁰ , a salt of the compound AH represented by the general formula (3) can also be used. There is no restriction | limiting in particular as an acid in the salt which can be used, An inorganic acid or an organic acid may be sufficient.

In the reaction formula (1), the reaction can be performed using a condensing agent. The condensing agent that can be used is not particularly limited, and examples thereof include N, N′-dicyclohexylcarbodiimide, 1,1′-carbonylbis-1H-imidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, Examples thereof include hydrochloride, 2-chloro-1,3-dimethylimidazolium chloride and the like.
When using a condensing agent, it is 1-2 mol equivalent with respect to the compound represented by General formula (2) as a usage-amount of a condensing agent, Preferably it is 1-1.2 mol equivalent.

  When a solvent is used in the reaction formula (1), the solvent is not particularly limited and may be an inorganic solvent or an organic solvent. Specifically, for example, water; alcohols such as methanol, ethanol, propanol and butanol; halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as benzene, toluene and xylene; fats such as hexane and heptane Group hydrocarbons such as dimethylformamide (DMF), dimethylacetamide (DMA), dimethylsulfoxide (DMSO), 1,3-dimethyl-2-imidazolidinone (DMI), 1-methyl-2-pyrrolidone (NMP), etc. Examples include aprotic polar solvents; ethers such as ethyl ether, isopropyl ether, 1,2-dimethoxyethane (DME), tetrahydrofuran (THF) and dioxane; nitriles such as acetonitrile and propionitrile.

In the reaction formula (1), the amount of the thiophenecarboxylic acid represented by the general formula (2) is 1 to 2 molar equivalents, preferably 1 to 1. with respect to the compound represented by the general formula (3). 2 molar equivalents.
Further, the reaction temperature and reaction time in the above reaction formula (1) can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. Moreover, reaction time is 0.01 to 50 hours, Preferably it is 0.1 to 15 hours.

  The method for producing a thiophenecarboxylic acid derivative of the present invention includes a step of reacting a compound represented by the following general formula (4) with a compound represented by the following general formula (3). That is, the thiophenecarboxylic acid derivative of the present invention can be produced by a reaction represented by the following reaction formula (2).

In Scheme ^(2), R ^1, R 2, ^{R 3} and A are as defined ^{R 1,} R 2, ^{R 3} and A, respectively, in the general formula (1), Y represents a leaving group.
As the leaving group represented by Y, a leaving group usually used in a condensation reaction can also be used in the present invention. Specifically, for example, halogen atoms typified by chlorine atoms, alkoxy groups typified by methoxy groups and ethoxy groups, aryloxy groups typified by phenoxy groups, acyloxy groups typified by acetyloxy groups, methoxycarbonyloxy Examples thereof include an alkoxycarbonyloxy group represented by a group, an arylcarbonyloxy group represented by a phenylcarbonyloxy group, N-hydroxysuccinimide, 1-hydroxybenzotriazole, and an imidazole group.

  In the reaction formula (2), by reacting the compound represented by the general formula (4) and the compound represented by the general formula (3) in the absence of a solvent or in a solvent, the general formula (1) The represented thiophenecarboxylic acid derivative can be produced.

The reaction represented by the reaction formula (2) can be carried out in the presence of a base.
The base is not particularly limited, and may be an inorganic base or an organic base. Specific examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide, alkali hydrides such as sodium hydride and potassium hydride. Metals, alkali metal alcoholates such as sodium methoxide and sodium ethoxide, alkali metal oxides such as sodium oxide, carbonates such as potassium carbonate and sodium carbonate, tripotassium phosphate, trisodium phosphate, dipotassium monohydrogen phosphate And phosphates such as disodium monohydrogen phosphate, acetates such as sodium acetate and potassium acetate, and organic bases such as pyridine, 4- (dimethylamino) pyridine, triethylamine and diazabicycloundecene.

When a base is used in the reaction formula (2), the amount of the base used is not particularly limited. In particular, when an organic base is used, it can be used as a solvent in the reaction formula (2).
When a solvent is used for the reaction represented by the reaction formula (2), the same solvent as that used in the method represented by the reaction formula (1) can be used as the solvent.

In the reaction formula (2), the amount of the compound represented by the general formula (4) is preferably 1 to 2 molar equivalents, more preferably 1 to 1 with respect to the compound represented by the general formula (3). .2 molar equivalents.
Further, the reaction temperature and reaction time in the reaction formula (2) can be changed in a wide range. In general, the reaction temperature is preferably -20 to 200 ° C, more preferably 0 to 100 ° C. The reaction time is preferably 0.01 to 50 hours, more preferably 0.1 to 15 hours.

The compound represented by the general formula (4) can be produced by a conventional method using the thiophenecarboxylic acid represented by the general formula (2). For example, the thiophene carboxylic acid represented by the general formula (2) is converted to thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride. , 1,1′-carbonylbis-1H-imidazole and the like.
Further, the compound represented by the general formula (4) is usually reacted with the thiophenecarboxylic acid represented by the general formula (2) with alcohols such as methyl alcohol and ethyl alcohol in the absence of a catalyst or a catalyst. It can also be manufactured by the law.

  The disinfectant of the present invention contains at least one thiophenecarboxylic acid derivative represented by the following general formula (5) as an active ingredient. Thereby, an excellent plant disease control action, particularly an excellent control action against rice blast can be exhibited.

In General Formula (5), R ⁵¹ and R ⁵² are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or the number of carbon atoms. 1-6 haloalkoxy groups, C1-C6 alkylthio groups, C1-C6 haloalkylthio groups, C1-C6 alkylsulfinyl groups, C1-C6 haloalkylsulfinyl groups, C1 Represents a -6 alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group. However, at least one of R ⁵¹ and R ⁵² represents a haloalkyl group having 1 to 6 carbon atoms.

R ⁵³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group.

A ⁵⁰ represents OR ⁵⁴ , SR ⁵⁵ , NR ⁵⁶ R ⁵⁷ or NR ⁵⁸ NR ⁵⁹ R ⁶⁰ ,
R ⁵⁴ and R ⁵⁵ are each independently an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, carbon An alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted heteroaryl group Represents an optionally substituted aryl group or an optionally substituted heteroaryl group.

R ⁵⁶ and R ⁵⁷ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with An alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms It is. Here, R ⁵⁶ and R ⁵⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.

R ⁵⁸ , R ⁵⁹ and R ⁶⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁵⁹ and R ⁶⁰ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.

In the present invention, from the viewpoint of a plant disease control effect, R ⁵¹ is preferably a haloalkyl group having 1 to 6 carbon atoms, R ⁵² and R ⁵³ are preferably hydrogen atoms, and R ⁵¹ is 1 to 6 carbon atoms. It is more preferable that R ⁵² and R ⁵³ are hydrogen atoms, R ⁵¹ is a fluoroalkyl group having 1 to 6 carbon atoms, and R ⁵² and R ⁵³ are hydrogen atoms. More preferably, A ⁵⁰ is NR ⁵⁶ R ⁵⁷ or NR ⁵⁸ NR ⁵⁹ R ⁶⁰ , and R ⁵⁶ and R ⁵⁸ are hydrogen atoms.

Specific examples and preferred ranges of the substituents represented by R ⁵¹ , R ⁵² , R ⁵³ and A ⁵⁰ in the general formula (5) include R ¹ , R ² , R ³ and A in the general formula (1). Specific examples and preferred ranges of each substituent represented are the same.
Moreover, the thiophenecarboxylic acid derivative represented by the general formula (5) can be produced by a production method similar to the production method of the thiophenecarboxylic acid derivative represented by the general formula (1).

  Moreover, the disinfectant of this invention contains at least 1 sort (s) of the thiophenecarboxylic acid represented by the said General formula (2) as an active ingredient. Thereby, an excellent plant disease control action, particularly an excellent control action against rice blast can be exhibited.

  There is no restriction | limiting in particular as a use of the disinfectant | microbicide of this invention, For example, it can use as industrial disinfectants for antiseptic | preservation, mold prevention, etc., agricultural / horticultural disinfectants, medical / disinfectant disinfectants, etc. In particular, the fungicide of the present invention is preferably used as an agricultural and horticultural fungicide because it exhibits a plant disease control action, particularly an excellent control action against rice blast.

  The fungicides of the present invention are, for example, vegetables originating from fungi belonging to alga fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes, fungi (Plasmodiophoromycetes) and other pathogenic fungi It can be used against a wide variety of plant diseases including fruit trees, rice, cereals, flower buds, turfgrass fields.

Next, specific disease names (bacterial names) for which the fungicides of the present invention can be used are listed as non-limiting examples.
For example, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), seedling blight caused by Pythium spp. (Pythium graminicola, etc.) Wheat powdery mildew (Erysiphe graminis f.sp.hordei; f.sp.tritici), leafy leaf disease (Pyrenophora graminea), net leaf disease (Pyrenophora teres), leaf blight (Gibberella zeae), rust disease (Puccinia) striiformis; P. graminis; P. econdite; P. hordei), snow rot (Typhula sp .; Micronectriella nivalis), naked smut (Ustilago tritici; U. nuda), eye spot (Pseudocercosporella herpotrichoides), cloud disease ( Rhynchosporium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), brown snow rot caused by Pythium spp. (Pythium iwayamai etc.),

Grape downy mildew (Plasmopara viticola), powdery mildew (Uncinula necator), black mildew (Elsinoe ampelina), late rot (Glomerella cingulata), rust (Phakopsora ampelopsidis), apple powdery mildew (Podosphaera leucotricha) , Black spot disease (Venturia inaequalis), spotted leaf disease (Alternaria mali), red star disease (Gymnosporangium yamadae), moniriosis (Sclerotinia mali), rot (Valsa mali), pear black spot disease (Alternaria kikuchiana), black star disease ( Venturia nashicola), red scab (Gymnosporangium haraeanum), pear plague (Phytophthora cactorum), peach blight (Sclerotinia cinerea), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), Ophthora (Phyopora sp) .), Oyster anthracnose (Gloeosporium kaki), deciduous leaf (Cercospora kaki; Mycosphaerella nawae), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsler) Sphaerotheca fuligin ea), anthracnose (Colletotrichum lagenarium), vine blight (Mycosphaerella melonis),

Tomato plague (Phytophthora infestans), seedling blight (Pythium vezans, Rhizoctonia solani), ring rot (Alternaria solani), leaf mold (Cladosporium fulvam), root rot (Pythium myriotylum, Pythium dissotocum), eggplant udon Erysiphe cichoracoarum, plague (Phytophthora infestans), brown rot (Phytophthora capsici), cruciferous vegetable black spot (Alternaria japonica), white spot (Cerocosporella barassicae), root-knot (Plasmodiophora brassicae), downy mildew Disease (Peronospora brassicae), white onion plague (Phytophthora porri), rust (Puccinia allii),

Soybean stem blight (Phytophthora megasperma), downy mildew (Peronospora manshurica), purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseololum), green beans (Colletotrichum lindemuthianum), peanut Black astringency (Mycosphaerella personatum), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), downy mildew (Peronospora pisi), potato plague (Phytophthora infestans), summer plague (Alternaria solani), Tea net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco red scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum),

Sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachtii), rose black spot (Diplocarpon rosae), downy mildew (Peronospora sparsa), plague (Phytophthora megasperma), powdery mildew (Sphaerotheca pannosa), chrysanthemum Brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana), plague (Phytophthora cactorum), strawberry powdery mildew (Sphaerotheca humuli), plague (Phytophthora nicotianae), fruit rot (Pythium ultimum), cucumber , Gray tomatoes (Botrytis cinerea) such as tomato, strawberry, grape, sclerotia (Sclerotinia sclerotiorum),

Shiva brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), curvularia leaf blight (Curvularia geniculata), rust disease (Puccinia zoysiae), herint sporium leaf blight (Cochiliobolus sp.), Cloud disease ( Rhynchosporium secalis), rice blast (Pyricularia oryzae), blight (Gaeumannomyces graminis), anthracnose (Colletotrichum graminicola), snow rot brown sclerotia nuclei (Typhula incarnata), snow rot black scab (Typhula ishikariensis) , Snow rot large sclerotia nuclear disease (Sclerotinia borealis), Fairy ring (Marasmius oreades, etc.), Pysium disease (Pythium aphanidermatum, etc.) etc. are mentioned.

  Among them, the thiophenecarboxylic acid derivative represented by the general formula (1) exhibits an excellent control effect particularly against rice blast (Pyricularia oryzae) and the like.

  The disinfectant of the present invention contains at least one thiophenecarboxylic acid derivative represented by the general formula (5) or a thiophenecarboxylic acid represented by the general formula (2). There is no restriction | limiting in particular as a usage form of the fungicide of this invention, For example, the chemical | medical agent process with respect to the above-ground part of a plant body, the chemical | medical agent process with respect to a rootstock and a seed, a soil process, etc. are possible.

The fungicide of the present invention can be used alone or mixed with other fungicides, insecticides, herbicides, agrochemicals such as plant growth regulators, soil improvers or fertilizers. It is also possible to use it as a mixed preparation.
The method for containing the thiophene carboxylic acid derivative and thiophene carboxylic acid in the fungicide of the present invention is not particularly limited, and the carrier includes a solid or liquid diluent even if the thiophene carboxylic acid derivative and thiophene carboxylic acid are contained as they are. You may contain in the composition mixed with. In the present invention, it is preferable to contain a thiophenecarboxylic acid derivative and a thiophenecarboxylic acid as the composition. The carrier as used herein means a synthetic or natural inorganic or organic substance formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transport and handling of the active ingredient compound.

Suitable solid carriers in the present invention include clays such as montmorillonite, kaolinite and bentonite, diatomaceous earth, white clay, talc, vermiculite, gypsum, calcium carbonate, white carbon, ammonium sulfate and other inorganic substances, soy flour, wheat flour Plant organic substances such as urea and urea.
Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene and cumene, paraffinic hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane, acetone, Ketones such as methyl ethyl ketone, ethers such as dioxane, tetrahydrofuran and diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, propanol and ethylene glycol, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide and 1-methyl-2-pyrrolidone And water.

  The disinfectant of the present invention can further contain various auxiliary agents. The adjuvant can be appropriately selected according to the purpose. For example, various adjuvants can be selected in consideration of enhancement of the bactericidal effect, the dosage form of the preparation, the application scene, and the like. These adjuvants can be used alone or in combination of two or more.

  Specific examples of the auxiliary agent include, for example, lignin sulfonate, alkylbenzene sulfonate, alkyl sulfate ester salt, polyoxyalkylene as an auxiliary agent for the purpose of emulsification, dispersion, spreading, wetting, binding and stabilization. Anionic surfactants such as alkyl sulfates and polyoxyalkylene alkyl phosphates; polyoxyalkylene alkyl ethers, polyoxyalkylene alkyl aryl ethers, polyoxyalkylene alkyl amines, polyoxyalkylene alkyl amides, polyoxyalkylene alkyl thioethers, Polyoxyalkylene fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester and polyoxypropylene polyoxyethylene block Nonionic surface active agents such as polymers; calcium stearate, lubricants such as wax, stabilizers such as isopropyl hydroperoxide diene phosphate; other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, the components of these adjuvants are not limited to the above.

  The content of the thiophenecarboxylic acid derivative represented by the general formula (5) and the thiophenecarboxylic acid represented by the general formula (2) in the fungicide of the present invention is usually 0.5 to 20% by weight in the case of a powder, 0.5 to 50% by weight, 0.5 to 90% by weight for wettable powders, 0.1 to 20% by weight for granules, and 0.5 to 90% by weight for flowable formulations. It is not limited to the content of.

  On the other hand, the carrier content in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, and 80 to 99% by weight for granules. And in a flowable formulation, it can be 10 to 90 weight%. The content of the adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, and 0.1 to 20 for granules. % By weight and 0.1-20% by weight for flowable formulations. In addition, the content of these carriers and the content of auxiliary agents are not limited, and can be appropriately adjusted in consideration of the physicochemical properties of the preparation, application scenes, and the like.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, “part” and “%” are based on mass.

Example 1
<Synthesis of N-cyclohexyl-2- (trifluoromethyl) thiophene-5-carboxamide (Compound No. 157)>
10 mL of thionyl chloride was added to 1.0 g of 2- (trifluoromethyl) thiophene-5-carboxylic acid, and the mixture was heated to reflux for 2 hours. After excess thionyl chloride was distilled off, benzene was added and low boiling point substances were distilled off under reduced pressure.
The residue and 0.62 g of cyclohexylamine were dissolved in 20 mL of dichloromethane, and 5 mL of a dichloromethane solution of 1.03 g of triethylamine was added dropwise under ice cooling. The mixture was stirred for 30 minutes under ice-cooling and then at room temperature for 4 hours. The reaction solution was poured into 200 mL of water and extracted twice with 300 mL of dichloromethane, and then the organic layer was dried over magnesium sulfate and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (dichloromethane / hexane) to obtain 1.2 g of the title compound as a light brown solid.

Example 2
<Synthesis of N- (2-bromopyridin-6-yl) -2- (trifluoromethyl) thiophene-5-carboxamide (Compound No. 202)>
1.0 g of 2- (trifluoromethyl) thiophene-5-carboxylic acid and 1.06 g of 2-amino-6-bromopyridine are dissolved in 20 mL of tetrahydrofuran, and 1-ethyl-3- (3-dimethyl) is cooled with ice. Aminopropyl) carbodiimide hydrochloride 0.98 g was added. After stirring at room temperature for 4 hours, 200 mL of dichloromethane was added and washed with water. The organic layer was dried over magnesium sulfate and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (dichloromethane / hexane) to obtain 1.5 g of the title compound as a light brown solid.

Specific examples of the compound of the present invention that can be produced in the same manner as in Examples 1 and 2 are shown below as compound numbers 1 to 416 represented by general formula (6) to general formula (9). Specific examples of the thiophenecarboxylic acid represented by the general formula (2) are shown below as compound numbers 417 to 457. In addition, Tables 1 to 3 show physical property values of some of the compounds.
In the following specific examples, Me is a methyl group, Et is an ethyl group, i-Pr is an isopropyl group, c-Hex is a cyclohexyl group, Bn is a benzyl group, Ph is a phenyl group, and vinyl is a vinyl group. Allyl represents an allyl group, propargyl represents a propargyl group, Ac represents an acetyl group, Bz represents a benzoyl group, and Naph represents a naphthyl group.

[Formulation examples and test examples]
Next, formulation examples and bactericidal activity test examples of the bactericide according to the present invention are shown. “Part” and “%” are based on mass.

(Formulation example 1) <Granule>
Compound No. 161 of the present invention compound 30 parts, bentonite 22 parts, talc 45 parts, Solpol 5060 (surfactant: Toho Chemical Co., Ltd. trade name) 3 parts and a small amount of antifoaming agent are uniformly kneaded, After granulating with a basket granulator, it was dried to obtain 100 parts of granules.

(Formulation example 2) <Granule>
After mixing 15 parts of the present compound of Compound No. (202), 60 parts of bentonite, 21 parts of talc, 1 part of sodium dodecylbenzenesulfonate, 1 part of polyoxyethylene alkylallyl ether and 2 parts of sodium ligninsulfonate, an appropriate amount was mixed. Water was added and kneaded uniformly, granulated with a basket granulator, and then dried to obtain 100 parts of a granule.

(Formulation Example 3) <Wetting agent>
Compound No. (179) 50 parts of the compound of the present invention, calcium carbonate 40 parts, Solpol 5039 (mixture of anionic surfactant and white carbon: trade name of Toho Chemical Co., Ltd.) and 5 parts of white carbon are uniformly mixed. This was pulverized into a wettable powder.

(Formulation example 4) <Wetting agent>
Compound No. (157) 30 parts of the present compound, kaolinite 63 parts, Solpol 5039 (mixture of anionic surfactant and white carbon: trade name of Toho Chemical Co., Ltd.) and 2 parts of white carbon are uniformly mixed. This was pulverized into a wettable powder.

(Formulation Example 5) <Emulsion>
20 parts of the present compound of Compound No. (14), 55 parts of xylene, 20 parts of N, N-dimethylformamide and 5 parts of Solpol 2680 (surfactant) were uniformly mixed to prepare an emulsion.

(Formulation example 6) <Flowable agent>
40 parts of the present compound of Compound No. (74), 5 parts of Solpol 3353 (nonionic surfactant: trade name of Toho Chemical Co., Ltd.), 5 parts of 1% aqueous solution of xanthan gum, 40 parts of water, 10 parts of ethylene glycol Among them, components other than the active component were uniformly dissolved, then the compound of the present invention was added and stirred well, followed by wet grinding with a sand mill to obtain a flowable agent.

(Formulation example 7) <Dust>
A compound was obtained by uniformly mixing 5 parts of the present compound of Compound No. (185) and 95 parts of clay.

(Test Example 1)
<Rice blast control effect test (dispersion test)>
A rice pot (variety: Koshihikari; 2 leaf stage) was sprayed with a wettable powder diluted to a concentration of 250 ppm of the compound of the present invention according to Formulation Example 4 and allowed to air dry. The plant was placed in an artificial weather chamber (setting conditions: 22 ° C., 12 hour dark light cycle) and spray-inoculated with a blast spore suspension. The weather chamber was kept at high humidity, and the survey was conducted 7 days after the inoculation. The control value was calculated by the following formula.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100

As a result, the following compounds showed a control value of 80 or more.
Compound numbers: 163, 191, 201, 212, 216.

(Test Example 2)
<Rice blast control effect test (initial activity test)>
In accordance with Formulation Example 4 for rice pots (variety: Koshihikari; 3 leaf stage), a diluting solution of the wettable powder prepared using the wettable powder of the compound of the present invention and the following comparative compound (A, B) was used as the prescribed drug. Irrigation treatment was performed so that the amount was 10 g (active ingredient per 10 ares). Three weeks after the drug treatment, a spore suspension of rice blast fungus was spray-inoculated, and the number of lesions was examined at a temperature of 25 ° C. under high humidity for one week. The control value was calculated by the following formula and evaluated according to the following evaluation criteria. The results are shown in Table 4.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100
-Evaluation criteria-
A: 80 or more B: 50 or more and less than 80 C: Less than 50

(Test Example 3)
<Rice blast control effect test (nursing box test)>
Grains prepared using the present compound and the above comparative compounds (A, B) according to Formulation Example 1 on rice seedlings (variety: Koshihikari; 2 leaf stage) grown in a rice seedling box (30 cm × 60 cm × 3 cm) Each agent was processed to 50 g per box. Three days later, they were transplanted to a 1/5000 aren Wagner pot and grown in a greenhouse. On the 30th day after transplantation, a spore suspension of rice blast fungus was spray-inoculated, and the number of lesions was examined at a temperature of 25 ° C. under high humidity for 1 week. The control value was calculated by the following formula and evaluated according to the following criteria. The results are shown in Table 5.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100
-Evaluation criteria-
A: 80 or more B: 50 or more and less than 80 C: Less than 50

(Test Example 4)
<Cucumber downy mildew control effect test (dispersion test)>
A cucumber pot (variety: Sagamihanjiro 2.0 leaf stage) was sprayed with a wettable powder diluted to 250 ppm according to Formulation Example 4 and allowed to air dry. It moved to the wet room installed in the greenhouse, and was spray-inoculated with the zoospore suspension of cucumber downy mildew. The investigation was conducted 7 days after the inoculation. The control value was calculated by the following formula.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100

As a result, the following compounds showed a control value of 80 or more.
Compound numbers: 147, 162, 163, 188, 212, 214, 216.

(Test Example 5)
<Cucumber powdery mildew control effect test (dispersion test)>
Cucumber udonko (variety: Sagamihanjiro 1 leaf stage) was sprayed with a dilute solution of wettable powder prepared to 250 ppm according to Formulation Example 4 and allowed to air dry. The powdery mildew fungus on the diseased leaves of cucumber that had been diseased in advance was inoculated with a paint brush evenly and inoculated, and the investigation was carried out 7 days later. The control value was calculated by the following formula.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100

As a result, the following compounds showed a control value of 80 or more.
Compound number: 147.

(Test Example 6)
<Wheat red rust control effect test (dispersion test)>
A wheat pot (variety: Sagamihanjiro 1.5 leaf stage) was sprayed with a dilute solution of wettable powder prepared to 250 ppm according to Formulation Example 4 and allowed to air dry. Wheat red rust spores collected from diseased plants were spray-inoculated and placed in a dark place at 4 ° C. for 2 days, then moved to an artificial weather room at 18 ° C., and an investigation was carried out 8 days later. The control value was calculated by the following formula.
Control value (%) = (1−number of lesions in treated area / number of lesions in untreated area) × 100

As a result, the following compounds showed a control value of 80 or more.
Compound number: 213.

From the above results, the fungicide containing the thiophenecarboxylic acid derivative of the present invention exhibits an excellent plant disease control action.

Claims (10)

A thiophenecarboxylic acid derivative represented by the following general formula (1).

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms.
R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group.
A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ .
R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.
R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms. The thiophenecarboxylic acid derivative according to claim 1, wherein R ¹ is a haloalkyl group having 1 to 6 carbon atoms, and R ² and R ³ are hydrogen atoms. The thiophenecarboxylic acid derivative according to claim 2, wherein R ¹ is a fluoroalkyl group having 1 to 6 carbon atoms. The thiophenecarboxylic acid derivative according to claim 3, wherein A is NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ , and R ⁶ and R ⁸ are hydrogen atoms. It is a manufacturing method of the thiophenecarboxylic acid derivative of any one of Claims 1-4, Comprising: The compound represented by following General formula (2), and the compound represented by following General formula (3) The manufacturing method of the thiophenecarboxylic acid derivative including the process of making it react.

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms.
R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group.
A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ .
R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.
R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms. It is a manufacturing method of the thiophenecarboxylic acid derivative of any one of Claims 1-4, Comprising: The compound represented by following General formula (4), and the compound represented by following General formula (3) The manufacturing method of the thiophenecarboxylic acid derivative including the process of making it react.

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms.
R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group.
A represents OR ⁴ , SR ⁵ , NR ⁶ R ⁷ or NR ⁸ NR ⁹ R ¹⁰ .
R ⁴ is an alkyl group having 8 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁵ is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. A C 1-6 alkyl group substituted with an optionally substituted aryl group, a C 1-6 alkyl group substituted with an optionally substituted heteroaryl group, optionally substituted An aryl group or an optionally substituted heteroaryl group is represented.
R ⁶ and R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with Represents an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms Here, R ⁶ and R ⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.
R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁹ and R ¹⁰ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.
Y represents a leaving group. ] A bactericide containing as an active ingredient at least one thiophenecarboxylic acid derivative represented by the following general formula (5).

[Wherein, R ⁵¹ and R ⁵² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ⁵¹ and R ⁵² represents a haloalkyl group having 1 to 6 carbon atoms.
R ⁵³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group.
A ⁵⁰ represents OR ⁵⁴ , SR ⁵⁵ , NR ⁵⁶ R ⁵⁷ or NR ⁵⁸ NR ⁵⁹ R ⁶⁰ ,
R ⁵⁴ and R ⁵⁵ are each independently an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, carbon An alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted heteroaryl group Represents an optionally substituted aryl group or an optionally substituted heteroaryl group.
R ⁵⁶ and R ⁵⁷ each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. , An optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aryl group having 1 to 6 carbon atoms, an optionally substituted heteroaryl group Carbon substituted with an alkyl group having 1 to 6 carbon atoms, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkylaminocarbonyl group, arylaminocarbonyl group or carboxy group substituted with An alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms It is. Here, R ⁵⁶ and R ⁵⁷ may be bonded to each other to form a heterocyclic group having 2 to 5 carbon atoms.
R ⁵⁸ , R ⁵⁹ and R ⁶⁰ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 6 carbon atoms. A cycloalkenyl group, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with an optionally substituted aryl group, and a carbon number substituted with an optionally substituted heteroaryl group 1-6 alkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, alkylaminocarbonyl groups Or represents an arylaminocarbonyl group. Here, R ⁵⁹ and R ⁶⁰ may combine with each other to form a heterocyclic group having 2 to 5 carbon atoms.   The disinfectant according to claim 7, which is used for agriculture and horticulture. A fungicide containing as an active ingredient at least one thiophenecarboxylic acid represented by the following general formula (2).

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms. A haloalkoxy group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. An alkylsulfonyl group, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group or a nitro group is represented. However, at least one of R ¹ and R ² represents a haloalkyl group having 1 to 6 carbon atoms.
R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A haloalkylthio group, an alkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, a halogen atom, a cyano group, or Represents a nitro group]   The fungicide according to claim 9, which is used for agriculture and horticulture.